The Best Small Towns in Hawaii to Visit (or Even Move To)
Nestled on the western coast of Maui, the charming town of Lahaina serves as a vibrant gateway to Hawaiian history and art, just a 45-minute drive from Kahului. Once the capital of the Hawaiian Kingdom, its Front Street teems with restored wooden storefronts and galleries showcasing local artists. Visitors stroll along the harbor, where the iconic Lahaina Banyan Tree—a sprawling canopy covering nearly an acre—offers shade and a gathering place for community events. The Lahaina Historic Trail invites exploration of sites tied to whaling-era tales and royal legacies, providing rich context to the town’s unique blend of cultural heritage and seaside charm. Early mornings or late afternoons are ideal for quiet walks when the light softens and the heat eases.
Further north on the Big Island, the town of Hawi in the Kohala district lies about 30 minutes from the Kona airport, perched amidst rolling hills and lush pastures. This small community pulses with a creative energy, evidenced by its artisan shops and cafés offering farm-to-table delights, many featuring locally grown macadamia nuts and coffee. The nearby Pololu Valley Lookout offers a breathtaking panorama of rugged cliffs and black sand beaches, with a steep but rewarding trail descending to the shore. Hawi’s tranquility and access to natural wonders make it a magnet for those seeking both artistic inspiration and outdoor adventure, particularly in the crisp mornings of the drier season.
On the island of Kauai, the town of Hanalei sits on the North Shore, about 40 minutes from Lihue Airport, framed by emerald mountains and a crescent-shaped bay famed for its surf breaks. The Hanalei Pier and Beach Park provide a relaxed scene for swimming or paddleboarding, while the nearby Hanalei Valley Lookout reveals taro fields spilling down to the river, a vivid reminder of ancient Hawaiian agriculture still practiced today. Hanalei’s quaint shops and eclectic eateries reflect a laid-back, bohemian vibe. Visiting during the winter months brings larger waves and surf competitions, while summer rewards with calm waters perfect for snorkeling and kayaking.
Over on Oahu, the laid-back town of Kailua lies on the island’s windward coast, about 30 minutes east of Honolulu. Kailua Beach Park’s powdery white sands stretch for two and a half miles beneath swaying palms and turquoise waters ideal for kayaking or stand-up paddleboarding. The nearby Lanikai Pillboxes Trail offers a short but steep hike with sweeping views of the Mokulua Islands, a favorite photo spot at sunrise. Kailua’s small-town feel contrasts with the nearby urban sprawl, boasting charming boutiques, farmers’ markets, and local eateries specializing in fresh seafood and shave ice. The trade winds cool the area consistently, making mornings and late afternoons perfect for outdoor activities year-round.
On Molokai’s north shore, the rustic village of Maunaloa sits near the midpoint of the island, about an hour’s drive from Molokai Airport. It’s a place where time seems to slow, and the spirit of old Hawaii lives on through traditional fishing and farming. The Maunaloa Forest Reserve offers easy hikes amid native koa and ‘ōhi‘a trees, with birdwatchers often spotting endangered species like the ‘apapane. The nearby Kalaupapa National Historical Park, accessible by mule ride or hike down the steep cliffs, tells a poignant story of Hawaii’s past with Hansen’s disease patients and stands as a testament to resilience and community. Visiting in the dry season ensures clearer trails and views of the remote coastline.
On the southeast coast of the Big Island, the tiny town of Pahoa lies about 45 minutes from Hilo, surrounded by a landscape shaped by recent lava flows. Pahoa’s Old Hawaii vibe is enriched by eclectic shops and cafés along its wooden boardwalks, where the energy of an artists’ colony is palpable. Just a short drive away, the Lava Tree State Monument preserves a forest of lava molds of ancient trees, creating a surreal lunar landscape. The nearby Red Road Scenic Drive, named for its distinctive iron-rich volcanic soil, winds along the coast past tide pools and waterfalls. Rainy season brings lush greenery and the dramatic contrast of black lava against vibrant flora, making this an unforgettable setting for exploration.
On Lanai, the town of Lanai City is a peaceful outpost about 20 minutes from Lanai Airport, offering a glimpse of plantation-era architecture surrounded by pine trees—unusual in tropical Hawaii. The Lanai Culture & Heritage Center provides insights into the island’s diverse history, from native Hawaiian roots to its role in pineapple cultivation. Lanai City’s compact layout invites leisurely strolls to cozy cafés and shops selling locally made crafts. For outdoor enthusiasts, the Munro Trail—a 12-mile dirt road that climbs to nearly 3,000 feet—offers sweeping views of Maui, Molokai, and the Big Island on clear days. Visiting during the cooler winter months is ideal, as the altitude brings refreshing breezes and clearer skies.
Finally, in the heart of Kauai’s South Shore lies the town of Koloa, about 20 minutes from Lihue Airport, steeped in plantation history. The Koloa Heritage Trail guides visitors through historic sugar mill sites, old churches, and charming neighborhoods that evoke a bygone era. Nearby Spouting Horn Park features a natural blowhole where ocean waves force water through lava tubes, creating impressive geysers of spray. Koloa’s botanical gardens and farmers’ markets showcase the island’s rich agricultural bounty. The drier season, from April to October, enhances access to outdoor sites and lends sunshine to this colorful town’s celebrations and festivals.